Triethylamine → 1-(Diphenylmethyl)azetidin-3-one

HRID 1689267Notes

Reaction equation

HRID 1689267 reaction equation
C(N(CC)CC)C.[CH:8]([N:21]1[CH2:24][CH:23]([OH:25])[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.S(=O)(=O)=O.N1C=CC=CC=1>CS(C)=O>[CH:8]([N:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

Triethylamine (24.7 mL) was added to a solution of 1-benzhydrylazetidin-3-ol (5 g) in DMSO (25 mL). A solution of pyridine sulphur trioxide (18 g) in DMSO (65 mL) was added dropwise and the mixture stirred at 20° C. for 90 minutes. The mixture was poured onto ice/water and extracted twice with ethyl acetate, the combined organics were washed three times with brine before being dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 2% triethylamine in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 2.9 g.

Workup

  1. additionThe mixture was poured onto ice/water
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organics were washed three times with brine
  4. dry with materialbefore being dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-f7599b4ea6a8475eb8aad115af9eeca5
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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